Methyl 2-chloro-1H-indole-3-carboxylate

Base Information

• Chemical Name: Methyl 2-chloro-1H-indole-3-carboxylate
• CAS No.: 152812-42-5
• Molecular Formula: C10H8ClNO2
• Molecular Weight: 209.632
• ChEMBL ID: CHEMBL4862487
• DSSTox Substance ID: DTXSID40598951
• Nikkaji Number: J2.494.224D
• Wikidata: Q82494771
• Mol file: 152812-42-5.mol

Synonyms:Methyl 2-chloro-1H-indole-3-carboxylate;152812-42-5;2-CHLORO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER;CHEMBL4862487;SCHEMBL5137730;DTXSID40598951;YODYXZOJWGXFSQ-UHFFFAOYSA-N;Methyl 2-chloroindole-3-Carboxylate;BDBM50577592;Methyl2-chloro-1H-indole-3-carboxylate;DA-17824;CS-0371045

Chemical Property of Methyl 2-chloro-1H-indole-3-carboxylate

Chemical Property:

• Melting Point: 183℃ (ethyl acetate hexane )
• Boiling Point: 365.6±22.0 °C(Predicted)
• PKA: 13.82±0.30(Predicted)
• PSA: 42.09000
• Density: 1.381±0.06 g/cm3(Predicted)
• LogP: 2.60790
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 209.0243562
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

98% ^*data from raw suppliers

Methyl2-chloro-1H-indole-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(NC2=CC=CC=C21)Cl

Technology Process of Methyl 2-chloro-1H-indole-3-carboxylate

There total 5 articles about Methyl 2-chloro-1H-indole-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

3-methoxycarbonylindole (942-24-5) → methyl 2-chloro-1H-indole-3-carboxylate (152812-42-5)

Guidance literature:

With N-chloro-succinimide; In N,N-dimethyl-formamide; for 1h;

DOI:10.1055/s-0031-1289732

Reference yield: 74.0%

methyl 3-chloro-3H-indole-3-carboxylate (254995-84-1) + N-(3-bromophenyl)benzylamine (213814-61-0) → methyl 2-(benzyl(3-bromophenyl)amino)-1H-indole-3-carboxylate + methyl 2-hydroxy-1H-indole-3-carboxylate + methyl 2-chloro-1H-indole-3-carboxylate (152812-42-5)

Guidance literature:

With trichloroacetic acid; In chloroform;

DOI:10.3390/molecules26196039

Reference yield: 27.0%

methanol (67-56-1) + 3-methoxycarbonylindole (942-24-5) → methyl 2-chloro-1H-indole-3-carboxylate (152812-42-5)

Guidance literature:

With N-chloro-succinimide; at 20 - 75 ℃; for 2h;

DOI:10.1021/acs.jmedchem.1c01077

upstream raw materials:

3-methoxycarbonylindole

sodium carbonate

methyl 3-chloro-3H-indole-3-carboxylate

N-(3-bromophenyl)benzylamine

Downstream raw materials:

C₁₇H₁₅N₃O₄

1-(3-(5-methyl-2-nitro-5H-indolo[2,3-b]quinolin-11-ylamino)propyl)-3-phenylurea

1-(3-(2-methoxy-5-methyl-5H-indolo[2,3-b]quinolin-11-ylamino)propyl)-3-phenylurea

1-(3-(5-methyl-2-(trifluoromethyl)-5H-indolo[2,3-b]quinolin-11-ylamino)propyl)-3-phenylurea

Refernces

• 1、 Zaienne, Daniel,Willems, Sabine,Schierle, Simone,Heering, Jan,Merk, Daniel. "Development and Profiling of Inverse Agonist Tools for the Neuroprotective Transcription Factor Nurr1". . p. 15126 - 15140. Retrieved 2021/10/25.
• 2、 Gan, Zongjie,Hu, Bin,Song, Qiao,Xu, Yungen. "Convenient chlorination of some special aromatic compounds using N-chlorosuccinimide". experimental part. p. 1074 - 1078. Retrieved 2012/05/04.